2-alkoxy-5-monosubstituted barbituric acids.



, 1,038,102. 80 Drawing.

X "acids of -the formula;

- (R is an a l R a substituent e. 9. CH C2H59 8,

UNITED-STATES PATENT oFrIoE.

in; momma, or trimaran), GERMANY, Assicmon 'ro ransnnmnmxsuvpmi. ramn. mums. a 00., or ELBERFELD, summar A coaroaa'rzon or (manner.

' a-hnxox -s-monosuns'rrrurnn nanm'rtmxcearns.

To" all whomit may concern: Be it known that I, MAx' ENGELMANN,

doctor ofrphilosophy, chemist, citiaen of the German I Barbituric Acids, of which the following is .aspe'cificatiori.

My invention concerns 4,, .CH C,H which have proved to be'.valuable soporifics, an" average dose being from i to 1; gram. The 'process for their production consists in treatlngthe ethers of isourea of theformulaz' (R'a substitucnt e. g. alkyl or aralkyl) or,

their salts with monosubs'tituted malonyl -pounds beingv converted 'by treating them with acids-into the 5-monoalkylor arylbarbituric acids.

3 the ethylether of isourea hydrochlorid:

In order to. illustrate the .new 4 process (BeHchteder-Deutachen ohmacken eta.

schaft, vol 33, 1900, p. 810.) are dissolved in 300 parts of water and 100p'arts of ethylmalonylchlorid dissolved in- 1000 parts of *p benzene are added. 'While cooling and stirring 280 parts of caustic soda lye (33 per cent.) are-poured to this solution until the mixture reacts alkaline. When the reaction is'complete the mixture is acidulated with acetic acid. The -2-ethoxy-5-ethyl-barbituric acid se arates in a white crystalline shape.

It is a ter drying recrystallized from alcohol. It'melts at 211 C. It is rather slightly soluble in cold water but easily the {product-ion of the hitherto unknown 2-alkoxybarbituric fipecifloationof Letters ratent. Patented Sept. 10, 1912. Application filed December 9, 1911.

Serial No; 664,890.

soluble alkalis and acids. By heating the ether with an acid e. g.' HG] it is converted into' the 5-ethylbarbituric acid. For this purpose 10 parts of the .ether are heated with 50 parts of a strong hydrochloric acid. on the water bath chloroethyl beingdi'sem.

The ethylbarbituric acid'thu's 'ob- The 2- gaged. tamed is. crystallized from water.

ethoxy-5-benzylbarbituric acid melts at 202 0., the 2-ethoxy-5-phenyl-barbituric acid melts at 218 C. Instead of the ethylether other derivatives e. g. isourea-methyl-ether or isoureabenzyl-ether can also be used.

- I claim l. The herein described '2-a1koxy-barbituric acids" having most probably the formula:

being crystalline powders; being converted,

into mono-substituted barbituric acids by treatment witha hot acid; andbeing' valuable soporifics, substantially as described.

-2. The herein described Q-aIkoXy-ba'rbituric acids,- having most, probably the formula:

, N OO ROC/' din-R \N do in which R alkyl, and R'=an alkyl group. being crystalline powders; being converted "into mono-substituted barbit-uric acids by treatment with a hot acid; and being valuable soporifics, substantially as 'described; h

3. The herein described 2-et-hoXy-5-ethy1- barbituri'c acid being a white crystalline owder melting at 211 C. diflicultlysoluble 111 cold water, easily soluble in alkalis and in acids; and being a valuable soporific, substantially as described. a

In testimony whereof I have hereunto set my hand inthe presence of two subscribing Witnesses: MAX ENGELMANN. [1 s.]

Witnesses:

' HELEN NUFERi ALB n'r'j NUFER. 

